If The Boss Only Knew

You know how the saying goes "When the cat is away, the mice will play." Have you ever back stabbed a co-worker, peer, or EVEN your boss? Do you involve yourself in political game playing, office manuvering, or one-upsmanship games to advance your job position? Are you secretly gunning for the boss's job? Have you setup a fellow co-worker to take an embarrassing hit? Have you positioned yourself as an expert in subject matter you know absolutely nothing about? Have you thrown a fellow co-worker under the bus to secure a promotion? Have YOU been thrown under the bus?

Maybe your office place dealings are more sexual in nature.. Have you been involved in an office place fling with a co-worker behind your bosses back? Did your office place sexcapades lead you to a promotion, or ultimately get you canned? Adult Confessions is the place to share all the juicy details. Your boss will never be the wiser! ;-)

— If The Boss Only Knew
—

Straight Male / 23

My boss thinks everything is fine and dandy in his marriage. He's so fucking arrogant, he actually believes his twenty nine year old wife Jenny, enjoys having sex with his fifty five year old small cock. She tells me if he wasn't loaded, which he is, she wouldn't be within five miles of his cock. She's his second wife and he genuinely believes she's faithful to him. Jenny's a real fine looking woman, and is always at the gym. Which is where most of the men who've fucked her since they got married, have met her. That's because Jenny is a dirty cock loving slut. And this boy just so happens to have a really big cock. And when I say she's a dirty slut, I mean it. She loves nothing more than to be fucked in her mouth, pussy and up her arsehole. And she loves it rough too.
We first fucked at the Christmas party last year. She cornered me in the function room at the golf club, where my boss is a senior life member, after donating a lot of money to improve the club. She asked me if the rumour was true about me. She'd spoken to a temp who'd let her know I'd fucked her on and off for a few months, telling Jenny I was well endowed. Pulling me outside in the cold night air, I was practically dragged over to the second green where she took out my cock and blew me, before she leaned against the flag pole and had me fuck her from behind. I swear I've never fucked a woman who wanted sex so badly. By the time I came inside her pussy, she'd climaxed twice, squirting both times all over my cock and balls and the green. Back inside, she was so calm telling her husband she'd shown me the facilities as I'd shown interest about becoming member. He smiled at his wife and looked at me like I was his new best friend. Little did he know later on when he asked me to give her lift, as he wanted to stay late taking a taxi home, that I'd be fucking his wife's arsehole in his very expensive car.
Most weeks now when I'm not with my girlfriend, Jenny and I get together when and where we can to have sex. I know I'm just a young guy with a big cock to her. But then again, she's just my bosses wife who happens to be one hell of a dirty slut.

I am a bisexual cross dressing sissy. Some call me a trap. But that is limited mostly to my social life. At work I dress in jeans, flannel plaid shirt and keep my long hair back in a pony tail. Some people shave Monday through Friday and let themselves go on the weekend. I do the opposite. I grow out my whiskers Monday through Friday and on weekends I shave close, put on make-up and can mostly just about pass as a girl though not quite as easily as I could when I was in school.

So I work at a warehouse and my boss is O.K. I guess. I do data entry and do final checks on outgoing merchandise. So I work with carriers a lot and the pickers of course. My boss spends most of his time in the office but comes out to the floor from time to time.

None of that really is worth talking about except for the fact that I bumped into my boss at a cross dressing party last week. Except he didn't know it. You see, when I go drag I don't look anything at all like myself when not dressed. But he didn't do a good job disguising himself. I recognized him immediately. At one point at the party he got on his knees in front of me and requested to choke on my cock. So I lifted up my skirt and pulled down my panties and stuck my 7 inch cock in his mouth. He sucked me until I came in his throat.

My boss is a woman, and for a while I used that as an excuse to relax a bit in the office, not worry about my appearance as much. Which I couldn't do when I worked for a man. If I let my appearance slip he'd tell me I looked tired or start ignoring me altogether, and it's actually why he hired someone younger than me with half the qualifications but a shorter skirt and bigger tits before he even told me I was being let go for "poor productivity."

An yway so working for her I felt much more secure, she wasn't about to fire me for skipping makeup one day, and that's still true.

But one day I felt like dressing up for myself, wore higher heels, dug out a tight skirt, and left a few extra buttons undone on my blouse.

I caught her sneaking looks all day. Mostly while I was facing away, but she nearly broke a pen when I brought in something that needed her signature and leaned down next to her to put it in front of her. After which, she "accidentally" dropped said pen which rolled away from the desk then asked me to pick it up for her. Then she told me to hold her calls for about an hour.

So that's how I found out my boss was a lesbian.

I decided to use this to my advantage. I started dressing like that every day, standing closer to her when I was at her desk or with her in the elevator, "accidentally" brushing up against her. One day I pretended to cry at my desk, then gave her a story about my boyfriend leaving me for someone prettier (I hadn't had a boyfriend in years) when she asked what was wrong. She reassured me that I was beautiful, he was a jerk, and gave me a hug, then we talked for a minute or two about men being awful.

After that I started talking to her more when we weren't busy. At one point she asked me about my relationships. I think she was trying to be casual but it didn't really work, she asked me about my past boyfriends then kind of stuttered when she added "or girlfriends, whichever."

I told her "well I've only ever been with men, but I mean every woman thinks about other women too, right?" She seemed to agree pretty eagerly.

About a month later I was looking for an opportunity to ask for a raise. Our work was done for the day and we were talking and I brought it up. She said she wasn't sure. I went and sat on the edge of her desk, I told her I really needed the money to take care of my bills.

She said she'd look into it.

I rubbed her leg with mine and I asked if there was any way I could help her decide.

She said she might be able to work something out, but she needed to evaluate my performance.

I got down and sat in her lap sideways, I told her she seemed pretty satisfied with my performance so far. She didn't say anything, so I kissed her.

She pulled me closer, ran her hand over my thigh, then broke the kiss and told me to go lock the door.

Once I did, she asked me if I was just doing it for the raise. I told her no, which wasn't a total lie. I was mostly doing it for the raise, but honestly even though I'm not into women I had to admit the situation was turning me on anyway.

She slipped out of her pants and had me eat her out first. I was kinda grossed out being face to lips with another woman's business, but once I dug in I got used to it. She said I wasn't that good, and if I expected a raise she expected me to get better at it.

Then she laid me back on her desk and ate me out. It was honestly the best orgasm I'd had probably my whole life. But she wasn't done, she had me strip down to my stockings and lay on her desk while she played with me. Kissed me, fondled me, fingered me.

I stayed naked in her office until the day was out, only a few people called for business over the phone.

Since then I've gotten that raise. When we have free time we don't always fuck, but I've gotten better at eating out, she started keeping toys in her desk. Even when we're just talking we sit closer together, sometimes she has me put my feet in her lap and she massages them. Sometimes if she's busy but I'm not she likes me to be in the office with her. Today she was filling out paperwork, she gave me a vibrator and told me to use it until she needed me to do something.

She wants me to consider moving in with her. She has a nice house and she lives alone, and it's not like I've really got anything going on outside of work, so I'm considering it. I consider myself straight, but I can make an exception. And besides, if I can do it, why not go from being just a secretary and living in a shoebox to also being a sugar baby and living in a nice house?

When I was in college my dorm mate and I were friends well still are but I know a secret he don't know. Almost every weekend we would go to parties and somehow he would get his hands on some drugs and pass out or go loopy (depending on the type of drug he gets). I take us back to our room which is hard cause this guy is huge all muscle, over six feet tall sports guy. I throw him on his bed and I crash on mine. Sometimes on those nights he wakes me up thinking we're still att a party and somehow mistakes me as a girl, crawls into my bed and proceeds to push his luckily average dick into my ass without lube and fucks me. So here we are in our room me trapped in my bed under my hulk of a friend who is plowing my ass in his drugged up state thinking he's got himself a girl from one of our classes, always calls me different names when he fucks me.

Sometimes its the nerd Suzan, or the cute lunch lady chelsie, or some girl from his hometown. But either way I'm enjoying his escapades not knowing he's fucking his friends ass and unloading his spunk into me or sometimes on me if he's just so eager, then he passes out on top of me. Then I gotta fight him limp body off mine and throw his ass into bed. Next day he starts bragging to me how he got some pussy last night at the party and keeps telling me I should loose my virginity soon or I will have a hard time getting any later in life. (Heh arogent prick)

Well few years later and here we are we both got families of our own, we work at the same factory, I'm head of maintenance and he is the son of the CEO who writes my checks.... and I see how funny it is that he's all redneck hating on faggets, this and that, but only I know how much his dick really liked my ass when he is drugged out of his mind ;)

This story is about a woman I work with. She's 53 and has worked at the Nursing home since she finished high school. I'm a man age 48 who works in the maintenance department. A job I had to take last year when my plant closed down.

She's head of the best floor in the nursing home, the rich part. I found out she gives some of the old men blow jobs for money. She gave me a few for free to keep me quiet. She tells me in the past she has done things for both men and women. From setting things up to preforming oral on both, to getting in bed with men having sex any way they like.

Started early for her and it never stopped. She said a man paid her to show him her naked body, then from there it went to anything, giving satisfaction to some rich lesbians. One of those lesbians left her a bit of money in her will. Said she liked how she treated her in the final years.

Her hair's pure white, the platinum blond she calls it. What pubic hair she has is thin and perfectly white. She said some men liked to see if the curtains matched the carpet.

Dad is the boss and his favorite salesman is in from out of town once each month. He's a
fantastic looker and usually we all go to the theater before a late dinner. Dad
and mom are up front and I sit with our visitor in the back, usually jerking
him off under his coat and/or sucking his thick cock with my head supposedly on his lap
on our way home late from dinner. That's all we've done so far but he's terrified
of us getting caught by dad. Whatever, to be continued. I usually get
what I want. A good mouthful will have to do for now.

Several years ago when Craig's List was good for random hookups, I had a pretty hot encounter at my job in New York City.

I worked in a small office that had two companies on each floor, which were separated by a long hallway. My office was on the 8th floor.

One Friday afternoon, my boss was in meetings all day and the other two people were out all day.

I learned about Craig's List and started checking it out. I think it was called Casual Encounters (?)

I posted about being in my office alone and looking for someone to come and make out.

I got a response and we started emailing back and forth.

She said she had one other guy she was about to go meet but he hadn't heard back from him. So if she didn't hear from him in the next 5 minutes she would come meet me.

My cock was hard just thinking about this potential situation. Here I was alone in the office with a possibility that a co-worker could come back in trying to have this girl come in and hook up.

She emailed me back saying she would come to me. I asked what she looked like but all she said was guys never complained about her. I thought that was a bad sign but I said to myself, Fuck it, see what happens and even if she's not good looking, the experience could be great.

So I'm waiting for the buzzer to ring and my dicks getting hard in anticipation. The buzzer sounds, I buz to let her in. I stand in the hallway waiting for the elevator and she comes out.

She was ok looking, a little chubby, glasses and wearing like a hippy dress but she had really big tits.

She came in and I closed and locked the door. She sat down and we started talking a little bit. Then I just leaned over towards her and started kissing her. We made out and eventually stood up.

I gently moved her over to the wall next to the door and thought, Holy shot, someone could come back to the office and here I am making out with some random girl in the office. It excited me even more.

We were really going at it passionately and I pulled up her dress and pulled her panties down and started fingering her. At that point she unbuckled my belt, pulled my pants down and started blowing me while I continued to finger her wet pussy.

So I'm standing against the wall and she is bent over getting fingered while giving me the most amazing blowjob.

She stops for a second and let's put this little squeaky moan and says Oh fuck, im Cumming! She grips my ass and then continues sucking my cock. Im so fucking hard, I say, But m gonna cum thinking she may just stop and jerk me off but she keeps going and I shoot my load in her mouth. I put my head back against the wall and try to catch my breath.

She pulls up her panties and asks where the bathroom is.

She comes out, I walk her to the elevator and tell her how amazing that was. She gives me a quick kiss and says goodbye.

We emailed a few times after that but soon after I got a girlfriend and I never saw her again.

I have such great memories of that exciting office blowjob and I never looked at that wall in the office the same way again.

On Wednesday my boss leaves early. One Wednesday a co-worker came to me told me that he had wanted me every since he first noticed that I had on my bra. He asked if I wear panties or pantyhose. I told him, "I was hoping you would notice some feminine anything about me, and yes I am wearing panties that match my bra and Pantyhose right now.

He asked if I was gay? I said, "No, I am a girl inside and I am totally feminine. He said that he noticed my sexy walk my feminine jester's. I said, "It's noticable"? He said that he had never seen anything manly about me. Thank you for letting me know.

Then my heart started racing when said it. He said that he really wanted to fuck my sexy girl ass. He said that I have a bigger ass and hips than any girl he has dates and it is very feminine specially with the tight pants really let us all know you liked guys.

He took my hand like I was a woman. He lead me to his van. It had a bed. We went in and I began to rub his cock. I said that I can feel through your pants that your cock is much bigger than mine. He asked to see it. I pulled my pantyhose and panties. He said that he could not believe how small it is. I told him that I have to potty sitting down like the girl that I am. It is a lot lower than a real man cocks, I consider it my clitoris.

I opened his pants and pulled out his big cock. I was excited. I began to lick it paying close attention to the head. Then I take all can of this enormous cock. I gag on it several times. He shot cum in my mouth and it was more than my mouth could hold. I had cum dripping from my lip and he pulled out and shot my face. Of course he had nothing to clean my face. He said, "You look so pretty with my cum on your face.

I tried to sneak back in and run to the bathroom and hope nobody sees me. Well I was seen by 7 people who said, "We knew you were gay". I just kept going to the bathroom. I cleaned up and thought about how much I enjoyed it and his cum tastes so good.

He said that next wWednesday I would bring girl clothes and make them sexy. I became submissive to his very masculine Dom personality.

Today is next Wednesday and I have sexy lingerie to show off my feminine body. He liked last week. I am also on testosterone blockers and estrogen and soon comes my boobs. I hope he fucks me and puts his huge cock all the way in. Please please fuck me.

So there's this guy I've had a serious case of wet pussy for since I first started working with him. He's insanely handsome and muscular, just how I like 'em ;) Married, as luck would have it. I don't like to mess with people's relationships, and I was dating somebody, so I kind of just let it stay a fantasy and never acted on it, but secretly pictured him naked and wondered about his dick size every time I ran into him. I could always see him checking out my ass while trying to not get noticed checking out my ass. And I kept wondering if he would eat said ass lol. Fast forward to a few weeks ago, we got to talking after a few drinks, and the talk immediately turned sexual. I was dying inside...it's finally happening!! aaaahhh!!! No touching happened that night, but I went home and played with my pussy all night, must have cum 3 or 4 times that night, I was dripping wet at the possibility of finally feeling what it's like to ride this dick...

Over the next couple of days, we are texting back and forth all damn day, turning each other on. Well, mostly he was the one getting turned on because it's harder for girls to get aroused at text messages but whatever. You know how it goes, talking about the things we like sexually what we do and don't do... He told me he loved to eat pussy (and ass!). Now I won't lie, I read that and basically jumped up and down. Men, hear me out. Every man should both be willing to eat pussy, and also know HOW to eat pussy. This is a delicate flower, not a goddamn burrito, technique is everything. Don't be slobbering on that shit for 5 seconds then patting yourself on the back, because you know if we're down there sucking your dick, we're down there for a while! Anyways back to the story, knowing that he loves eating pussy was all I needed to hear, married or not, I was going to have him. He also told me he was a big freak, could go all night long, he loved to please, yada yada yada. He built up my expectations like no other, and I believed him. His wife was a sexy, sexual-looking woman, I was like no way a woman like that would have put up with some disappointing sex.

So by this point, fucking him was all I could think about, it was driving me crazy. I invited him over, and about 5 minutes in, I realized I had made a huge error of judgement. This guy tries to jam his entire tongue in my mouth repeatedly (slow the f down), grabs my breast like he's trying to rip it off my body (ouch- there is no grabbing in sex, just lick my nipples damn) and immediately does this annoying thing guys do- grab your hand and guide it to their dick.

I'm a grown ass woman, you think I don't know how to find a dick? If I'm not grabbing your dick yet, it's because I'm still not turned on and not in the zone, and you need to slow down for a second to let me catch up with your arousal. So I pull my hand back, instead of catching the hint, dude stands up puts one leg up on the couch and presents his erect penis to my face. Like LOOK I HAVE A DICK I wanted to scream. What happened to "I'm sensual, i'm a pleaser, I love eating pussy" and all that? I was slowly accepting that this was going to be incredibly different from everything we had talked about. I explicitly told this guy what I liked, I'm not shy by any means, and he was blowing through every single thing I told him.

I put his dick in my mouth and give it maybe 50% effort. I give fire head but I'm also equality-driven, so when I get no head, I start giving head half-assedly. He tried to choke me with his dick, which was pretty big btw (the only part of my fantasy that came true!) and I'm like whoa, you still haven't yet earned choking privileges my friend. So I push him away and lay back and spread my legs and invite him over. He dives in like the Goblet of Fire is hidden in my pussy and he needs to retrieve it with his tongue. Now guys, enthusiasm is appreciated, but pussy eating should never be rough, and just like blowjobs, no teeth shall be involved, ever. The clitoris is VERY sensitive, always start slow and gentle, you can implement your turbo tongue a little later. Seriously, that shit hurts like hell if done wrong, which is exactly what was happening to me. I was pulling away so hard I was basically cutting off my own oxygen with my head smushed into the couch. Another tip, if a girl is pulling away, it's not pleasurable. Period. Don't mistake her moans and screams of frustration for those of pleasure.

He does this for roughly 2 minutes and comes back up and shoves his dick in my mouth. OMG. I do that for 10-15 mins and he is so damn quiet all I can hear is the sounds of myself being choked with big penis repeatedly. Quiet guys, I get you, but I'm very vocal and I like my men vocal, quiet just creeps me out a little. But to each their own. We get to fucking, and we have no rhythm. NONE. With some people you just find your groove from the first second, not this guy. No rhythm, and he's still so quiet that if it was the other way around I would have felt like I was fucking a sleeping person. And I'm not even wet because remember, nothing was really done on that front. There was so little chemistry I just wanted him to finish so he could leave and I could mourn this 5-year old fantasy. I was thinking of which bottle of wine to open after he leaves. He gives it a solid 20-30 pumps and he's done and tells me how this was amazing and beyond his expectations and wow and whatever. Fuck me, really?? And just when I thought it was over, he starts jerking off, without me. Now I'm not going to stop him, but what? My poor little unsatisfied pussy was begging for attention, and you decided to play with your own dick? Fine. He cums in my mouth, I swallow it, and immediately get up, wash up, and get dressed. Hint, hint. After what seemed like forever of him sighing and saying "wow", he finally left. I sat there on my bed for 30 minutes contemplating what the hell just happened, then brought out my vibrator, watched 2 lesbians lick pussy, and finally had my orgasm that's been 5 years in the making.

If you made it this far thanks for reading, I just needed to vent! Clearly me and this guy had zero chemistry, maybe he is great with other women, who knows. I wonder if his wife is getting her dick on the side. Final thing to say is: a sexually satisfied girl will go to great lengths for your sexual satisfaction! Treat your girl right in the pussy department ;)

I hired into a prestigious publishing office as a management trainee. They started me on the mail cart
and today with email most of it is strictly junk mail but for the brief time I had the job, I loved it.
As the weeks went by I discovered that we had two office "punchboards" as they were called. That is, two
ladies who fucked everyone freely. One was 19 and the other 56.

Delivering my daily morning junk mail I caught the 19 year old being fucked so many times in everyone's office that I wondered if that was actually her job. The 56 years old one, a senior editor, was nowhere near as active but I saw her giving a few blow jobs through the months. I felt rather superior because when they spotted me they tried to look normal and I found it hysterical.

The teenager never wore underwear and carried a bag with paper tissues. Some of the guys suggested I give her a pop but I found her a bit too used for my taste. Call me silly and get it over with, eh? Oddly enough, the 56 year old was more to my fancy. She had silver hair and was statuesque, with a great smile. What drew me physically was her
wide hips flowing into a giant, round ass and s narrow waist. She was also tall.

When I was dropping off her junk mail she would always smile at me and glance at my package...that grew larger
in time, in her presence, as we became more familiar with each other. Once, I noticed her knees slightly apart and opening and closing. I did not pick this up as any kind of signal but found it interesting,

My mail cart was put away in the supply room and I soon discovered that was the teenager's "base" finding
her there, fucking a number of men (one at a time) through the months. Mostly it was a quickie type done doggie
style as no one was in a hurry to be discovered fucking at work. One day, she sat next to me in the lunch room
knowing full well that I had walked in on her a number of times no matter how she tried to finesse it. I said,
"What if you get caught?" She answered, who by? I'm fucking them all, even the company CEO, I love it. I'm not going to stop until I'm outta here. Some days six guys blow their loads into me, I can feel their pulsing cum into me right now, I love it. I've now done all three floors." She looked me up and down, (I'm 6'4") and said, "Why not get yourself a sample, you must be hung like a hippo." She spoke of all of it as if it was like she was just playing a card game.

Days after that, I recall vividly, I pushed the cart into the older lady's office. She said, "Oh do me a favor and just toss all that junk here in the dust bin. She pushed her chair away from her desk, still sitting in it, and looking down, I noticed she wore nothing by her high heel shoes from her waist down. She had a giant grin. I got an instant erection. She reached for my throbbing rod, rubbed it under my pants and said, "Lock my door" which transformed my erection into steel.

We spend the next 30 minutes scoring every point on the sex chart. Best of all, she loved doggie and had those hot,
wide hips, a powerful looking ass. Bent over from behind, she was a fucking dream even at her age. I left the publishing house for a much better deal three months later but by the time I left I had scored the middle-aged lady
over 100 times and the teenager zero. I know, you'll think me an idiot. That's fine. At some point I'm going call my elderly office lover and ask for some more action on the outside. Then I will fuck her silly.